Warm winter getaways are the easiest way to hit reset when the days get short and the coat comes out of the closet. This season the booking data is unusually clear about where people are heading, so instead of guessing, you can plan your December-to-February escape around the places travelers are actually searching for and booking right now.
The appetite is real. Tripadvisor’s Winter Travel Index found that 60% of travelers are planning winter trips, 45% say they are traveling more this winter than last, and winter bookings on the platform jumped 45% year over year. Expedia’s search data and Airbnb’s winter report point at the same sunny corners of the map. Below are eight warm-weather escapes for winter 2026-27, why each one is trending, when to go and what to throw in your bag.
1. Key West, Florida
If you want one of the easiest warm winter getaways with no passport required, Key West is the obvious starting point. In Tripadvisor’s winter report, Key West ranked among the top domestic destinations for U.S. travelers, alongside New York City, Las Vegas and Orlando, and it is the only beach town in that group. It also showed up on the global list of top picks for domestic travelers.
Why it is trending: it delivers a genuine island feel on U.S. soil, which matters when 54% of winter travelers are committing to stays of five nights or more, according to the same Tripadvisor survey. A long week in the Keys is simpler to pull off than a long-haul flight.
Best time to go: January and February, once the holiday rush has cleared. Pack: linen shirts, sandals you can walk Duval Street in, reef-safe sunscreen and a light layer for breezy evenings on the water.
2. Cancún and Playa del Carmen, Mexico
For U.S. travelers going abroad this winter, Mexico’s Caribbean coast is the clear favorite. Tripadvisor’s list of top international destinations for U.S. travelers is led by Cancún and Playa del Carmen, and Cancún also ranked among the top global picks for international travelers overall.
Why it is trending: short, direct flights from most major U.S. cities, turquoise water and a range of stays from all-inclusive resorts to walkable town rentals. It is also a great base if you care about experiences: Tripadvisor reports that 93% of travelers see experiences as important to their travel budget, and cenote swims and Mayan ruins are a day trip away.
Best time to go: the drier winter months, avoiding the peak Christmas and New Year week if you want better rates. Pack: quick-dry clothing, water shoes for the cenotes and a breathable tee for long days out. Our premium cotton t-shirts are built for exactly this kind of hot, humid, on-the-move day.
3. Cabo San Lucas, Mexico
Cabo San Lucas rounded out Tripadvisor’s top international picks for U.S. travelers, and it offers a very different vibe from the Caribbean side. Think desert mountains meeting the Pacific, dramatic rock arches and a big nightlife scene.
Why it is trending: it is one of the easiest international warm winter getaways from the western U.S., and it suits the travelers Tripadvisor describes as putting relaxation first, a priority for 51% of Baby Boomers and 51% of Gen X in its survey.
Best time to go: winter is peak season, so book early. Pack: a wide-brim hat, polarized sunglasses and a light long-sleeve layer for sun protection on boat days.
4. The Dominican Republic
The Dominican Republic made Tripadvisor’s shortlist of top international winter destinations for U.S. travelers, and it rewards anyone who wants more than a pool chair. Punta Cana brings the classic resort beaches, while the Samaná Peninsula and the colonial streets of Santo Domingo add nature and culture.
Why it is trending: good-value beach resorts plus plenty to do. Tripadvisor found that the top winter activities are cultural sightseeing (38%), nature exploration (37%), shopping (31%) and road trips (28%), and the DR covers most of those in one trip.
Best time to go: mid-January through February for settled weather and fewer holiday crowds. Pack: swimwear, a sun hat, bug repellent for jungle excursions and comfortable shoes for Santo Domingo’s cobblestones.
5. Florida’s Gulf Coast: Fort Walton Beach and Anna Maria Island
Two Gulf Coast names jump out of this year’s data. Expedia named Fort Walton Beach one of its 2026 Destinations of the Year, with searches up 45%, and Airbnb listed Anna Maria, Florida among its trending warm winter getaways in the U.S., alongside Bay St. Louis, Mississippi, Hermosa Beach, California and Lafayette, Louisiana.
Why it is trending: families and longer stays. Airbnb found that nearly half of winter travelers vacation with family and a third of families travel for seven nights or more, and a beach house on the Gulf fits that brief perfectly. Airbnb also reported that all of the top 10 destinations for travelers aged 60 and over are in Florida.
Best time to go: late February, when Gulf Coast days start to warm up. Be honest with yourself here: the northern Gulf is mild rather than hot in midwinter, so it suits walking, fishing and sunsets more than all-day swimming. Pack: layers, a light jacket for evenings and a cap for long beach walks.
6. Costa Rica
Costa Rica is the pick if your idea of warm winter travel includes volcanoes, cloud forests and wildlife as well as beaches. Airbnb highlighted San José, Costa Rica, as one of its trending gateway destinations for winter, the kind of hub travelers use as a launchpad for road trips to the coasts and the mountains.
Why it is trending: it fits the growing appetite for active, experience-led trips. Tripadvisor found that 84% of travelers prioritize planned activities, and Costa Rica is built for zip lines, surf lessons, hot springs and guided rainforest hikes.
Best time to go: the heart of the dry season on the Pacific side. Pack: a rain shell for the cloud forest, trail shoes, a daypack and a sun hat. Our premium travel hats earn their place on beach days and rainforest trails alike.
7. Phu Quoc, Vietnam, and the Thai Coast
If you have the time for a long-haul trip, Southeast Asia is where the search growth is. Expedia named Phu Quoc, Vietnam, a 2026 Destination of the Year with searches up 53%. Airbnb also flagged Prachuap Khiri Khan, Thailand, the coastal province that includes Hua Hin, as a trending winter gateway, and Tripadvisor listed Bangkok among the top global destinations for international travelers this winter.
Why it is trending: long, affordable stays and a real sense of discovery. Pair a few nights in Bangkok with a week on the Gulf of Thailand, or fly into Phu Quoc for white-sand beaches and night markets.
Best time to go: the dry season, which lines up neatly with the Northern Hemisphere winter. Pack: breathable cotton, a light cover-up for temple visits and a packable bag for market hauls.
8. Hobart, Australia
Here is the wildcard among this year’s warm winter getaways: skip winter entirely by flying into someone else’s summer. Expedia named Hobart, Tasmania, a 2026 Destination of the Year with searches up 25%, and it was one of six destinations to earn Expedia’s Smart Travel Health Check, a sustainability assessment of how well a place can handle a surge of visitors.
Why it is trending: a food-and-wine scene, wild coastline and easy access to national parks, all in the Southern Hemisphere’s warm season during your December-to-February window.
Best time to go: January and February. Pack: Tasmanian summer can swing from beach weather to cool and windy in a day, so bring a warm layer alongside your tees and sunscreen.
Whichever you choose, keep your bag light so you can move easily. Our guide on how to pack a carry-on will help you fit a week of warm-weather outfits into one bag.
Frequently Asked Questions
What are the most popular warm winter getaways for 2026-27?
According to Tripadvisor’s Winter Travel Index, Key West, Cancún, Playa del Carmen, Cabo San Lucas and the Dominican Republic are among the top warm-weather picks for U.S. travelers. Expedia’s search data also highlights Fort Walton Beach (+45%) and Phu Quoc (+53%).
How long are people staying on winter trips this year?
Longer than you might expect. Tripadvisor found that 54% of winter travelers are committing to stays of five nights or more, and Airbnb reports that a third of families are traveling for seven nights or more.
Where can I find true summer weather in December, January or February?
Head to the Southern Hemisphere, where it is summer during the northern winter. Hobart, Australia, is a strong option: Expedia named it a 2026 Destination of the Year with searches up 25%.
Sources and Further Reading
- Tripadvisor Winter Travel Index Report (November 2025)
- Expedia: Where to Travel in 2026, Destinations of the Year (October 2025)
- Airbnb: Emerging destinations redefine winter travel this season (October 2025)
The best warm winter getaways are the ones you actually book, so pick your spot, lock in your dates and start packing for the sun. When you are ready to gear up for the trip, explore the full collection at Around The World In A Rush 👉 ✈️ 🌍
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